Oregon's Trails: The "great train robbery" that wasn't

State of Oregon Archives(From left) Ray, Hugh and Roy DeAutremont attempted a train robbery 86 years ago today
that was one of Oregon’s most notorius crimes. The brothers dressed up for this photo before
their trial in Jackson County in an effort to help their case.Of all the heinous crimes recorded in Oregon history, one invariably rises to the top.

It happened 86 years ago today, on Oct. 11, 1923, on a mountainside south of Ashland. The perpetrators were three criminally ambitious but inept brothers, 23-year-old twins Ray and Roy DeAutremont and brother, Hugh, 19.

"It's amazing that America is still fascinated with the crime," says Margaret LaPlante of Medford, author of the newly published "The DeAutremont Brothers, America's Last Great Train Robbery." "It's a story that just keeps going strong and probably always will."

The products of a large family that lived in various Western locales, the DeAutremont twins in summer 1922 found themselves in Oregon. They were destitute and discouraged by the prospect of earning honest livings, so they decided crime was the road to a life of luxury.

In Yacolt, Wash., they watched in frustration from across the street as a large Buick pulled up, blocking their view of the bank they planned to rob. Several men left the vehicle, robbed the bank, then sped off, leaving the two dumbfounded and still broke.

In Cannon Beach, they cased a candy store only to fall asleep in a nearby ditch, missing their chance to rob the elderly proprietor, who casually locked up and blissfully strolled off.

The twins, joined by Hugh, next decided train robbery would be a lucrative pursuit. They went to work in the woods, saved their money and equipped themselves. By summer's end in 1923, they were ready.

Their quarry was Southern Pacific Train No. 13 from Seattle to San Francisco, dubbed the "Gold Special" because it often carried bullion and lots of cash. The venue they chose was SP Tunnel No. 13 high in the Siskiyou Mountains.

The first part of their scheme came off as planned. Ray and Roy jumped aboard the train as it labored up the hill to the north end of the tunnel. They confronted the engineer and fireman with pistols and ordered them to halt the train just as the locomotive left the tunnel's south end, where Hugh stood armed with a shotgun.

Ray and Roy fastened a suitcase full of dynamite to the door of the mail car directly behind the engine tender and just inside the tunnel. They retreated to where they'd placed the detonator, and Roy hit the plunger.

Huge mistake.

The amount of dynamite they used was several times what was necessary to blow open the locked mail car. It blasted the car to bits, set fire to its contents and ripped the mail clerk to shreds.

Clark Williams, a reporter for The Oregonian, later observed that the mail car "had been reduced to kindling." The blast also blew out the windows of the passenger cars behind in the half-mile-long tunnel, filling them with acrid smoke.

"They didn't really do their research," LaPlante says. "They thought there was $40,000 aboard the train. There wasn't."

Panicked, the DeAutremonts fatally shot the engineer, fireman and a brakeman, then fled into the woods.

Nearby rail construction crews, hearing the blast, rushed to the scene, found the four dead men and summoned help. Before long, lawmen and vigilantes of every stripe were combing the hills for the brothers. Banner headlines erupted across the nation.

The brothers lay low in a forested hide-out for several days, then made their way to California, where they went their separate ways. It took what became known as the most extensive manhunt in U.S. history to bring them to justice.

"Over 9 million wanted posters were posted throughout the world," LaPlante says, "yet they managed to blend into society for almost four years."

Hugh was found serving under an alias with the U.S. Army in the Philippines. Ray and Roy were arrested in Steubenville, Ohio, where they were working. The three were returned to Jackson County for trial and sentenced to life in the Oregon State Penitentiary.

Hugh was paroled in 1958, moved to San Francisco and died of stomach cancer less than a year later. Roy suffered from schizophrenia and was transferred to the Oregon State Hospital. He was released in 1983 and died in 1984. Ray was paroled in 1961, lived in Eugene and died in 1984.

-- John Terry is a retired copy editor for The Oregonian and a member of the Oregon Geographic Names Board